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Fluorescent probe used for detecting glutathione as well as preparation method and application thereof

A technology of glutathione and fluorescent probes, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, biological testing, etc., can solve problems such as the difficulty in realizing specific detection of glutathione, and achieve easy promotion and application, excellent Responsive sensitivity, low-cost effect

Inactive Publication Date: 2015-06-17
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, most of the reported glutathione probes are interfered by amino acids that also contain sulfhydryl groups in organisms, such as cysteine ​​(Cysteine, Cys) and homocysteine ​​(Homocysteine, Hcy) (see J. Bouffard, Y.Kim, T.M.Swager, etc., A Highly Selective Fluorescent Probe for Thiol Bioimaging, Org.Lett., 2008, 10: 37-40; X.-D.Jiang, J.Zhang, X.Shao, etc., A selective fluorescent turn-on NIR probe for cysteine, Org.Biomol.Chem., 2012,10:1966-1968), it is difficult to realize the specific detection of glutathione in complex organisms

Method used

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  • Fluorescent probe used for detecting glutathione as well as preparation method and application thereof
  • Fluorescent probe used for detecting glutathione as well as preparation method and application thereof
  • Fluorescent probe used for detecting glutathione as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 2

[0067] Embodiment 2, the preparation of fluorescent probe Nap-GSH

[0068] Step a): Under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalene dicarboxylic anhydride to 100mL of anhydrous methanol, then inject 5.0mL of n-butylamine, and reflux at a reaction temperature of 120°C 10 hours. After the reaction was complete, needle-like crystals precipitated after standing overnight, filtered and washed three times with cold ethanol to obtain 4.40 g of intermediate N-n-butyl-4-bromo-1,8-naphthalimide (yield 84%).

[0069] Step b): Under an inert atmosphere, add 1.00g of N-butyl-4-bromo-1,8-naphthalimide and 3.94g of p-methylthiophenol into a 50mL three-necked flask, inject 20mL of butanol and 2.5 mL of diisopropylethylamine was refluxed for 10 hours at a reaction temperature of 140°C. After the reaction is complete, the reaction solution is poured into 200mL of ice water, a large amount of solids precipitate out, filtered, washed, and dried in vacuo to obtain N-n-butyl-4-(p-...

Embodiment 3

[0073] Embodiment 3, the preparation of fluorescent probe Nap-GSH

[0074] Step a): Under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalic anhydride to 100mL of anhydrous n-propanol, then inject 7.5mL of n-butylamine, at a reaction temperature of 80°C, Reflux for 5 hours. After the reaction was complete, needle crystals precipitated after standing overnight, filtered and washed three times with cold ethanol to obtain 4.60 g of intermediate N-n-butyl-4-bromo-1,8-naphthalimide (yield 87%).

[0075] Step b): Under an inert atmosphere, add 1.00g of N-n-butyl-4-bromo-1,8-naphthalimide and 0.38g of p-methylthiophenol into a 50mL three-necked flask, inject 20mL of diethyl Glycol monomethyl ether and 2.9 g of potassium carbonate were refluxed for 24 hours at a reaction temperature of 140°C. After the reaction is complete, the reaction solution is poured into 200mL of ice water, a large amount of solids precipitate out, filtered, washed, and dried in vacuo to obtain N-n-butyl...

Embodiment 4

[0079] Embodiment 4, the preparation of fluorescent probe Nap-GSH

[0080] Step a): Under an inert atmosphere, add 5.00g of 4-bromo-1,8-naphthalene dicarboxylic anhydride to 100mL of anhydrous n-butanol, then inject 10.0mL of n-butylamine, and at a reaction temperature of 70°C, The reaction was refluxed for 1 hour. After the reaction was complete, needle-like crystals precipitated after standing overnight, filtered and washed three times with cold ethanol to obtain 4.84 g of intermediate N-n-butyl-4-bromo-1,8-naphthoimide (yield 88%).

[0081] Step b): Under an inert atmosphere, add 1.00g of N-n-butyl-4-bromo-1,8-naphthalimide and 2.87g of p-methylthiophenol into a 50mL three-necked flask, inject 20mL of ethanol and 3.5 g of potassium hydroxide was refluxed for 1 hour at a reaction temperature of 100°C. After the reaction is complete, the reaction solution is poured into 200mL of ice water, a large amount of solids precipitate out, filtered, washed, and dried in vacuo to obt...

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Abstract

The invention discloses a fluorescent probe used for detecting glutathione as well as a preparation method and application thereof. According to the invention, 1, 8-naphthalimide is used for building a classical ICT system, a phenyl sulfone part is introduced to the position of 4-, the ICT effect of a probe molecule is regulated and controlled, and due to the strong attracting electron effect of the phenyl sulfone in the position of the 4-, the probe molecule self is free from fluorescence emission. In case of the existence of glutathione, the phenyl sulfone part can be replaced by the glutathione, further the intramolecular electron transfer from sulphur atom in the position of the 4- (from glutathione) to the 1,8-naphthalimide can be generated, moreover, the ICT effect enables the probe molecule to send out strong fluorescence. The fluorescent probe provided by the invention can realize detection to the glutathione in cells, and has the advantages of being convenient and simple to operate, low in cost, sensitive in response, easy for popularization and application and the like.

Description

technical field [0001] The invention belongs to the technical field of biological detection, and in particular relates to a naphthaleneimide-phenylsulfone derivative used as a glutathione fluorescent probe material and a preparation method and application thereof. Background technique [0002] Glutathione (GSH) is a tripeptide molecule composed of glutamic acid, cysteine ​​and glycine, and is the most abundant thiol-containing amino acid in the human body. In the living body, glutathione plays an important role in maintaining intracellular redox balance, intracellular signal conversion and regulation. Abnormality of intracellular glutathione concentration will lead to a series of physiological diseases, such as leukocyte loss, psoriasis, liver damage, cancer and AIDS, etc. (see L.A.Herzenberg, S.C.De Rosa, J.G.Dubs, etc., Glutathione deficiency is associated with impaired survival in HIV disease, Proc. Natl. Acad. Sci. USA., 1997, 94: 1967-1972). Therefore, quantitative an...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D221/14G01N21/64G01N33/68
Inventor 韩益丰杨成玉
Owner ZHEJIANG SCI-TECH UNIV
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